CN111925312B - Indolyl-substituted indole-3-ketone and synthesis method thereof - Google Patents

Indolyl-substituted indole-3-ketone and synthesis method thereof Download PDF

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CN111925312B
CN111925312B CN202010853543.3A CN202010853543A CN111925312B CN 111925312 B CN111925312 B CN 111925312B CN 202010853543 A CN202010853543 A CN 202010853543A CN 111925312 B CN111925312 B CN 111925312B
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CN111925312A (en
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姬小趁
符妹
黄华文
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Xiangtan University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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Abstract

The invention relates to indolyl-substituted indole-3-ketone and a synthesis method thereof. The invention is firstly adopted in PPh3Under the condition of a reducing agent, in the argon atmosphere, indole compounds and o-nitroalkyne compounds are converted into indolyl-substituted indol-3-one, so that the prepared indole compound has a stable molecular structure and excellent chemical properties. The reaction raw materials of the synthesis method are cheap and easy to obtain, and do not need to be pretreated; only acid and reducing agent are needed in the reaction, and metal catalyst is not needed, so that raw materials are saved, and the reaction cost is reduced; the whole reaction system is simple, the reaction condition is mild, reaction equipment is less, the experimental operation is simple and convenient, and the material source is wide.

Description

Indolyl-substituted indole-3-ketone and synthesis method thereof
Technical Field
The invention relates to indolyl-substituted indole-3-ketone and a synthesis method thereof, belonging to the technical field of organic compound synthesis.
Background
Indolyl-substituted indol-3-one is an important nitrogen-containing aromatic heterocyclic compound, and indol-3-one is an important natural alkaloid and a pharmacologically active compound. Indolenine phenols with a 2, 2-disubstituted indol-3-one core structure are found in a variety of drugs, such as halichromene a, LipidGreen, isatisine a.
Figure BSA0000217545290000011
However, these compounds require multiple reactions to be prepared, and the preparation process is complicated.
Disclosure of Invention
The invention aims to supplement the defects of the prior art, provides the indolyl-substituted indol-3-one with stable molecular structure and excellent chemical properties, and simultaneously provides the synthetic method of the indolyl-substituted indol-3-one with simple preparation process.
The technical scheme adopted by the invention for solving the technical problems is as follows: the invention provides indolyl-substituted indol-3-one, which has a general formula I:
Figure BSA0000217545290000012
wherein
R1Selected from:
hydrogen atom, halogen radical, alkyl, methoxy, cyano, nitro, ester group and aldehyde group.
R2Selected from:
methyl, phenyl.
R3Selected from:
hydrogen atom, methyl group.
R4Selected from:
cyclopropyl, phenyl, heteroaryl, alkyl halide.
The application also provides a synthetic method of indolyl-substituted indole-3-ketone, which uses PPh3The method is used as a reducing agent and comprises the following steps:
s1: fully mixing indole compounds, acetic acid, a reducing agent and an organic solvent in a reaction container;
s2: heating the reactants under the argon atmosphere;
s3: purifying to obtain indolyl-substituted indole 3-ketone.
The synthesis method of the application, the general formula of the indole compound is formula II:
Figure BSA0000217545290000021
wherein
R1Selected from:
hydrogen atom, halogen radical, alkyl, methoxy, nitro, ester radical, cyano and aldehyde group.
R2Selected from:
hydrogen atom, alkyl group, phenyl group.
R3Selected from:
hydrogen atom, methyl group.
In the synthesis method, the indole compound is selected from: indole, N-methylindole, 5-bromoindole, 5-iodoindole, 5-cyanoindole, 5-nitroindole, indole-5-carbaldehyde and indole-7-carboxylic acid methyl ester.
The synthesis method of the application, the general formula of the o-nitroalkyne compound is shown as formula III:
Figure BSA0000217545290000022
wherein
R4Selected from:
cyclopropyl, alkyl chloride, aryl or heteroaryl.
The synthesis method of the present application, wherein the o-nitroalkynes are selected from: 1- (cyclopropylethynyl) -2-nitrobenzene, 1-nitro-2- (phenylethynyl) benzene, 1-nitro-2- (p-tolylethynyl) benzene, 1- ((4-methoxyphenyl) ethynyl) -2-nitrobenzene, 1- ((4-bromophenyl) ethynyl) -2-nitrobenzene, 1- (3, 3-dimethyl-1-butynyl) -2-nitrobenzene, 1-nitro-2- (oct-1-ynyl) benzene, 1-nitro-2- (non-1-ynyl) benzene, 1- (5-chloropentynyl) -2-nitrobenzene, 2- ((2-nitrophenyl) ethynyl) thiophene, 3- ((2-nitrophenyl) ethynyl) pyridine.
In the synthesis method of the present application, the acid compound is selected from: acetic acid, phosphoric acid, trifluoroacetic acid, trifluoromethanesulfonic acid, tetrafluoroboric acid.
According to the synthesis method, the molar ratio of the indole compound, the o-nitroalkyne compound, the triphenylphosphine and the acid is 1.0: 1.8-2: 0.2-1.2: 0.5-1.2, and the reaction time is 8-16 h.
According to the synthesis method, the organic solvent is o-dichlorobenzene.
The beneficial effects of the prior art of the invention are as follows:
(I) the invention is in PPh3Under the reducing agent, in the argon atmosphere, the indole compound and the o-nitroalkyne compound are converted into an indolyl-substituted indole-3-ketone, and the prepared molecular structure is stable; (II) the reaction raw materials are cheap and easy to obtain, so that the environmental pollution and the reaction cost are reduced; (III) adding a wonderful stroke to the scientific research result; (IV) a one-pot method is adopted to directly and selectively synthesize the target product, the yield is high, and a large amount of development time and production period are saved; (VI) the process is scientific and reasonable, the operation is easy, the reaction steps are few, and the required equipment is few; (VII) it has wide raw materials, low investment, high output, and is easy for further mass production and popularization; the method has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple and convenient experimental operation, wide material sources and the like.
Drawings
In order to demonstrate the products of the invention, the invention provides nuclear magnetic hydrogen and carbon spectra of some of the examples.
FIG. 1-1 nuclear magnetic hydrogen spectrum of the product of example 2.
FIGS. 1-2 nuclear magnetic carbon spectrum of the product of example 2.
FIG. 2-1 nuclear magnetic hydrogen spectrum of the product of example 3.
FIGS. 2-2 nuclear magnetic carbon spectrum of the product of example 3.
FIG. 3-1 nuclear magnetic hydrogen spectrum of the product of example 4.
Figure 3-2 nuclear magnetic carbon spectrum of the product of example 4.
FIG. 4-1 nuclear magnetic hydrogen spectrum of the product of example 7.
FIG. 4-2 nuclear magnetic carbon spectrum of the product of example 7.
FIG. 5-1 nuclear magnetic hydrogen spectrum of the product of example 8.
FIG. 5-2 nuclear magnetic carbon spectrum of the product of example 8.
FIG. 6-1 nuclear magnetic hydrogen spectrum of the product of example 9.
FIG. 6-2 nuclear magnetic carbon spectrum of the product of example 9.
FIG. 7-1 nuclear magnetic hydrogen spectrum of the product of example 10.
FIG. 7-2 nuclear magnetic carbon spectrum of the product of example 10.
FIG. 8-1 nuclear magnetic hydrogen spectrum of the product of example 11.
FIG. 8-2 nuclear magnetic carbon spectrum of the product of example 11.
FIG. 9-1 nuclear magnetic hydrogen spectrum of the product of example 12.
FIG. 9-2 nuclear magnetic carbon spectrum of the product of example 12.
FIG. 10-1 nuclear magnetic hydrogen spectrum of the product of example 16.
FIG. 10-2 nuclear magnetic carbon spectrum of the product of example 16.
FIG. 11 is a reaction equation of the synthesis method of the present invention.
Detailed Description
The present invention will now be described in further detail with reference to the accompanying drawings. These drawings are simplified schematic views illustrating only the basic structure of the present invention in a schematic manner, and thus show only the constitution related to the present invention.
The reaction equation is:
Figure BSA0000217545290000041
examples 1 to 16
The synthesis method of the substituted indoles comprises the following steps:
step 1: adding indole compounds (specific substances are shown in table 1), acid (specific substances are shown in table 1) and triphenylphosphine-PPh into a reaction vessel3Adding a catalyst and an organic solvent (specific substances are shown in table 1) into a reaction vessel and uniformly mixing;
step 2: argon is pumped out of the reaction vessel for three times, the reaction vessel is stirred at 50-120 ℃ (preferably 90 ℃), the indole compound and the o-nitroalkyne compound are reacted in the solvent, and the time is selected from 8-16h, preferably 12h, and is kept as shown in the table 1;
and step 3: and (4) after the reaction is finished, purifying to obtain the product.
Table 1: examples 1-16 indole Compounds, Ornitryl acetylenes, acid and reducing agent molar ratios and reaction times
Figure BSA0000217545290000042
Figure BSA0000217545290000051
Is the mol ratio of indole compounds, o-nitroalkyne compounds, acid and reducing agent
And (3) detecting the conversion rate of the substances in the reaction vessel after the step (3) and performing nuclear magnetic resonance, wherein the results of some examples are as follows:
the nuclear magnetic data of the product of example 2 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ7.70(d，J＝7.7Hz，1H)，7.47(t，J＝7.7Hz，1H)，7.35(s，1H)，7.26(t，J＝6.6Hz， 1H)，7.20-7.06(m，2H)，6.90(dt，J＝17.9，7.5Hz，2H)，6.80(d，J＝8.2Hz，1H)，4.59(s，1H)，3.75(s，3H)，1.69-1.62 (m，1H)，0.76-0.64(m，1H)，0.54-0.31(m，3H)；13C NMR(100MHz，CDCl3，ppm)δ203.8，160.8，137.4，137.4， 128.7，125.4，125.1，121.9，121.1，119.5，119.5，119.2，113.6，112.5，109.5，67.2，32.8，16.0，2.2，-0.8.
the nuclear magnetic data of the product of example 3 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ8.10(s，1H)，7.63(d，J＝8.2Hz，1H)，7.52(d，J＝7.7Hz，1H)，7.41-7.25(m，7H)， 7.14(t，J＝7.6Hz，1H)，7.01(t，J＝7.6Hz，1H)，6.78(t，J＝7.4Hz，1H)，6.55(d，J＝8.2Hz，1H)，4.46(s，1H)，1.61- 1.54(m，1H)，0.27-0.01(m，4H)；13C NMR(100MHz，CDCl3，ppm)δ203.3，160.2，137.0，136.9，135.3，134.3，130.4，128.5，127.7，126.6，125.0，122.3，121.0，120.9，120.1，118.8，111.9，111.6，110.7，68.4，17.3，3.5，0.9.
the nuclear magnetic data of the product of example 4 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ8.38(s，1H)，7.72(d，J＝7.7Hz，1H)，7.51(t，J＝7.6Hz，1H)，7.20(t，J＝10.2Hz， 2H)，6.96-6.82(m，4H)，4.59(s，1H)，2.25(s，3H)，1.68-1.61(m，1H)，0.69-0.62(m，1H)，0.50-0.30(m，3H)；13C NMR(100MHz，CDCl3，ppm)δ204.3，161.0，137.5，135.0，129.0，125.2，125.1，124.3，123.8，121.1，119.3，119.0， 114.4，112.5，111.2，67.4，21.6，16.0，2.2，-0.8.
the nuclear magnetic data of the product of example 5 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ8.42(s，1H)，7.71(d，J＝7.7Hz，1H)，7.50(t，J＝7.7Hz，1H)，7.24(d，J＝2.7Hz， 1H)，7.16(d，J＝8.8Hz，1H)，6.92-6.81(m，2H)，6.74(dd，J＝8.8，2.4Hz，1H)，6.43(d，J＝2.4Hz，1H)，4.58(s，1H)， 3.46(s，3H)，1.68-1.62(m，1H)，0.71-0.62(m，1H)，0.48-0.33(m，3H)；13C NMR(100MHz，CDCl3，ppm)δ204.2， 161.1，153.9，137.6，131.7，125.2，125.0，124.9，121.3，119.4，114.9，112.4，112.4，112.2，101.0，67.4，55.1，15.5，2.0， -1.0.
the nuclear magnetic data of the product of example 6 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ8.61(s，1H)，7.71(d，J＝7.8Hz，1H)，7.59-7.48(m，1H)，7.26(s，2H)，7.20- 7.12(m，2H)，6.98-6.77(m，2H)，4.59(s，1H)，1.63-1.57(m，1H)，0.72-0.58(m，1H)，0.51-0.27(m，3H)；13C NMR(100MHz，CDCl3，ppm)δ203.9，160.8，137.9，135.3，126.6，125.4，125.2，125.1，122.0，120.7，119.6，114.7， 113.1，113.0，112.5，67.2，16.1，2.1，-0.7.
the nuclear magnetic data of the product of example 7 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.31(s，1H)，7.58-7.42(m，5H)，7.32-7.23(m，2H)，6.89(d，J＝8.2Hz，1H)， 6.75(t，J＝7.4Hz，1H)，1.70-1.60(m，1H)，0.69-0.58(m，1H)，0.50-0.41(m，1H)，0.36-0.26(m，1H)，0.17-0.07 (m，1H)；13C NMR(100MHz，DMSO-d6)δ202.8，161.4，137.8，135.8，129.1，128.1，127.8，125.5，124.4，118.7，117.4， 114.2，114.0，111.6，82.8，66.7，15.9，1.6，-0.9.
the nuclear magnetic data of the product of example 8 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.71(s，1H)，7.73(d，J＝2.4Hz，1H)，7.62-7.35(m，6H)，6.91(d，J＝8.2Hz，1H)， 6.76(t，J＝7.4Hz，1H)，1.73-1.60(m，1H)，0.68-0.56(m，1H)，0.50-0.40(m，1H)，0.39-0.24(m，1H)，0.20-0.05 (m，1H)；13C NMR(100MHz，DMSO-d6)δ202.3，161.3，138.5，137.9，126.96，124.9，124.7，124.5，123.9，120.7，118.5， 117.5，115.6，113.2，111.6，100.7，66.7，16.2，1.5，-0.8.
the nuclear magnetic data of the product of example 9 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.86(s，1H)，8.17(d，J＝2.2Hz，1H)，7.96(dd，J＝9.0，2.3Hz，1H)，7.80(s，1H)， 7.60-7.43(m，4H)，6.91(d，J＝8.3Hz，1H)，6.77(t，J＝7.4Hz，1H)，1.72-1..63(m，1H)，0.67-0.59(m，1H)，0.51- 0.42(m，1H)，0.39-0.30(m，1H)，0.18-0.10(m，1H)；13C NMR(100MHz，DMSO-d6)δ202.2，161.4，140.3，139.9， 137.9，128.1，124.5，124.1，118.4，117.6，117.4，116.7，116.6，112.3，111.7，66.7，16.1，1.5，-0.8.
the nuclear magnetic data of the product of example 10 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.22(s，1H)，7.73(d，J＝7.5Hz，1H)，7.63-7.44(m，4H)，7.37(d，J＝7.9Hz，1H)， 6.99(t，J＝7.7Hz，1H)，6.88(d，J＝8.2Hz，1H)，6.75(t，J＝7.4Hz，1H)，3.94(s，3H)，1.74-1.59(m，1H)，0.71-0.58 (m，1H)，0.53-0.42(m，1H)，0.39-0.26(m，1H)，0.19-0.05(m，1H)；13C NMR(100MHz，DMSO-d6)δ202.7，166.5， 161.3，137.8，135.1，126.8，126.2，125.2，124.4，123.9，118.7，118.4，117.3，115.2，112.6，111.6，66.6，51.9，16.0，1.6， -0.9.
the nuclear magnetic data of the product of example 11 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.64(s，1H)，9.76(s，1H)，7.81(s，1H)，7.68(d，J＝2.4Hz，1H)，7.61(d，J＝8.5Hz， 1H)，7.55-7.45(m，4H)，6.90(d，J＝8.2Hz，1H)，6.75(t，J＝7.4Hz，1H)，1.75-1.61(m，1H)，0.66-0.58(m，1H)， 0.52-0.44(m，1H)，0.37-0.30(m，1H)，0.17-0.09(m，1H)；13C NMR(100MHz，DMSO-d6)δ202.5，192.2，161.4， 140.3，137.8，128.4，126.5，124.9，124.5，124.3，122.0，118.6，117.5，116.7，112.5，111.7，66.9，16.2，1.6，-0.7.
the nuclear magnetic data of the product of example 12 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.12(s，1H)，8.38(s，1H)，7.50(q，J＝7.8Hz，4H)，7.40(d，J＝8.1Hz，1H)，7.34- 7.24(m，3H)，7.13-6.98(m，4H)，6.86(t，J＝7.5Hz，1H)，6.75(t，J＝7.4Hz，1H)；13C NMR(100MHz，DMSO-d6)δ 200.4，161.0，140.1，137.8，136.9，128.2，127.5，126.7，125.6，124.7，124.2，121.4，120.0，118.7，117.6，117.4，114.6， 112.0，111.8，70.7.
the nuclear magnetic data of the product of example 13 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.11(s，1H)，8.06-7.98(m，2H)，7.48-7.31(m，4H)，7.05-6.93(m，3H)，6.59(t， J＝7.3Hz，1H)，1.00(s，9H)；13C NMR(100MHz，DMSO-d6)δ202.7，161.1，137.4，136.8，127.3，125.5，124.2，122.3， 121.1，119.9，119.0，116.9，112.0，111.8，110.5，74.5，39.2，25.8.
the nuclear magnetic data of the product of example 14 are as follows:
1H NMR(400MHz，DMSO-d6)δ11.08(s，1H)，7.65(t，J＝8.0Hz，1H)，7.49-7.34(m，4H)，7.15(d，J＝8.2Hz，1H)， 7.05(t，J＝7.5Hz，1H)，6.97(t，J＝7.4Hz，1H)，6.89(t，J＝7.5Hz，1H)，3.57-3.35(m，3H)，2.11-2.05(m，2H)，1.88 -1.80(m，1H)；13C NMR(100MHz，DMSO-d6)δ203.4，164.8，138.0，137.5，125.8，124.7，123.8，122.1，121.6，120.7， 120.5，119.0，114.4，113.5，112.1，77.7，50.1，32.5，28.3.
the nuclear magnetic data of the product of example 15 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ8.38(s，1H)，7.69(d，J＝7.7Hz，1H)，7.48(t，J＝7.7Hz，1H)，7.28-7.08(m，5H)， 7.02-6.84(m，5H)，5.50(s，1H)；13C NMR(100MHz，CDCl3，ppm)δ199.7，160.2，144.1，144.1，137.8，136.8，127.5， 125.7，125.6，125.3，124.9，124.0，122.4，120.0，119.4，119.1，115.0，113.0，111.8，69.2.
the nuclear magnetic data of the product of example 16 are as follows:
1H NMR(400MHz，CDCl3，ppm)δ8.58(s，1H)，8.49(d，J＝4.6Hz，1H)，7.76(d，J＝8.0Hz，1H)，7.66(d，J＝7.7Hz， 1H)，7.56(td，J＝7.7，1.8Hz，1H)，7.44(t，J＝7.7Hz，1H)，7.21(d，J＝8.3Hz，1H)，7.14(t，J＝6.0Hz，2H)，7.05(t，J＝7.6Hz，1H)，6.98-6.90(m，2H)，6.87-6.81(m，2H)，6.73(s，1H)；13C NMR(100MHz，CDCl3，ppm)δ200.5，161.8， 157.4，148.4，137.6，136.8，136.7，125.5，125.0，123.7，122.9，122.5，122.2，120.5，119.8，119.7，119.5，115.7，114.0， 111.6，72.2.
TABLE examples 1-20 conversion and products of the reactions
Figure RE-GSB0000190007540000081
Figure BSA0000217545290000091
Figure BSA0000217545290000101
Figure BSA0000217545290000111
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (3)

1. The synthesis method of indolyl-substituted indol-3-one is characterized in that PPh is used3The method is used as a reducing agent and comprises the following steps:
s1: fully mixing indole compounds, o-nitroalkyne compounds, acid, a reducing agent and an organic solvent in a reaction vessel;
s2: heating the reactants under the argon atmosphere;
s3: purifying to obtain indolyl-substituted indole-3-ketone;
an indolyl-substituted indol-3-one, having the general formula I:
Figure FSB0000195110100000011
wherein
R1Selected from: hydrogen atom, halogen group, alkyl group, methoxy group,cyano, nitro, ester, aldehyde;
R2selected from: methyl, phenyl;
R3selected from: hydrogen atom, methyl group;
R4selected from: cyclopropyl, phenyl, heteroaryl, alkyl, haloalkyl;
the general formula of the indole compound is shown as formula II:
Figure FSB0000195110100000012
the general formula of the o-nitroalkyne compound is shown as formula III:
Figure FSB0000195110100000013
the acid is selected from: acetic acid, phosphoric acid, trifluoroacetic acid, trifluoromethanesulfonic acid, and tetrafluoroboric acid.
2. The synthesis method according to claim 1, wherein the molar ratio of the indole compound, the o-nitroalkyne compound, the triphenylphosphine and the acid is 1.0: 1.8-2: 0.2-1.2: 0.5-1.2, and the reaction time is 8-16 h.
3. The method of synthesis according to claim 1, wherein the organic solvent is ortho-dichlorobenzene.
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